Green’s Dictionary of Slang

1. the penis.

1988		Boogie Down Productions ‘Jimmy’ 🎵 Here is a message to the Super Hoes / Just keep in mind when Jimmy grows.
1993		Dr Dre ‘Fuck Wit Dre Day’ 🎵 It seems like you’re good for makin jokes about your jimmy.
2000		Ebonics Primer at www.dolemite.com 🌐 jimmy Definition: the male sexual organ. the penis. Example: I straight out waxed dat bitches ass last night, cuz my jimmy runs deep, know what I’m sayin.
2002		Sean Paul ‘Jukin Punny’ 🎵 Non-stop pressure till the jimmy ho bust, pop!

2. (US black/campus) a condom.

1990		Vanilla Ice ‘Ice Cold’ 🎵 I wore a jimmy that I slapped on.
1996		Eble Sl. and Sociability 123: Slang synonyms like jimmy, jimmy hat, party hat, sheepskins, and raincoat [...] serve to distance the harsh realities that make the protective device a subject of public language.
1997–2002		Hope College ‘Dict. of New Terms’ 🌐 jimmy n. Condom. ‘Make sure you take your jimmy on your date. You might get lucky.’.

3. (N.Z. prison) a firearm, a pistol.

2001

D. Looser Boobslang [U. Canterbury D.Phil. thesis] 95/2: jimmy n. a firearm, esp. a pistol.